Bucks offseason preview: Free agents, financial outlook & big decisions

The Bucks will most likely go over the second threshold of the luxury tax once they fill out all the roster spots. That will all but rule the taxpayer mid-level exception out and make it tough to find success in the trade market as well.

The team will have a new co-owner, so chances are the new guys will be more than willing to spend big bucks — no pun intended — to keep the team competitive for the time being. But they’re already coming off paying a franchise-record $83 million in tax penalties.

The front office most likely promised Giannis Antetokounmpo they’d continue to pay up to stay competitive throughout his prime before he agreed to sign that massive contract extension. So, again, they need to do whatever it’s in their power to re-sign Brook Lopez, Joe Ingles, and Jae Crowder.

Doing so, while also bringing in a couple of guys on veteran-minimum deals and signing a second-round pick would put them in the $125 million range in tax penalties. That equals to roughly $315 million in payroll alone.

The Bucks could be severely hampered in their ability to add talent midseason. They won’t be able to sign players waived unless their salaries are below the non-taxpayer mid-level exception, and those aren’t usually very good players.

The other option for the Bucks will be the less popular, but perhaps the one that makes the most sense from a financial standpoint. They can simply decide to blow the roster up and start back from scratch, at the risk of infuriating their generational player.

The only good part about that is that Giannis would be able to play alongside all his brothers and even some cousins if he also wants them to get paid, all because of that new brutal CBA and their historically high penalties for going over the luxury tax.

The Middleton dilemma

Of course, there’s also the Khris Middleton dilemma. The Milwaukee Bucks offseason plans 2023 must include Middleton for the reasons we already mentioned, but he’s also one of the backbones of this team, so he’s the kind of guy they need on the floor.

Before the start of the season, Middleton was a lock to opt out of the final year of his deal. He could either threaten to test free agency waters or actually do it, and he could make a case for finding himself a very lucrative deal out there.

That may no longer be the case. He’ll be 32 years old next season and is coming off an injury-riddled campaign in which he never truly got his footing. He doesn’t have a history of injuries, but Father Time is undefeated, and he’s due to make $40 million next season.

Middleton has thrived as Giannis’ No. 2. He’s an underrated defender who gives them plenty of length with his switches, and another offense facilitator who can put the ball on the floor and take it up the court as a secondary playmaker.

He’s also an efficient shooter from all three levels and a guy who knows the system well. It might be too late for him to try and find a similar role somewhere else, and we’ve seen that kind of story happen way too many times already: A veterean leaves to get paid on a bad team, just to be bought out midway through his contract.

Will he give up $40 million to sign another long-term deal, even if it pays him less by the year? Perhaps, but there won’t be much of a market for an aging wing coming off a career-worst season. Simply put, he needs the Milwaukee Bucks as much as the Milwaukee Bucks need him right now.